I haggle on every purchase I make, and I expect others to do the same.this is why I list my rentals at the top of market rate.

For that type of listing in that area, don't expect to be booked every night.

I do think parts will improve but like Payne Phalen I expect it to be a block by block situation. 

and if so is there a lower limit on the amount of cash flow I should expect on any given property?

As with many of us, I have fielded scores and scores of phone calls and have taken time to help those where I can with nothing expected in return

I guess my expectation is a little too high on this market, but I am actually shooting for 60 cents on a dollar. 

I don't expect any rentals during the snow melt season.  

What challenges should I expect going this route?

I would expect more like 70% to 75% LTV.  ($129,500 to $135,750) or ($136,500 to $146,250) depending on the appraised value.Shop around with local banks and credit unions for better deals.

I’m less familiar with the 4-plexes, but I would expect to be around break-even on the rent for 3 units (living in one) vs PITI.